Helix-sense tunability induced by achiral diene ligands in the chiral catalytic system for the helix-sense-selective polymerization of achiral and bulky phenylacetylene monomers

Macromolecules

Volumn 40, Issue 20, 2007, Pages 7098-7102

  Kaneko, Takashi ^a   Umeda, Yasuhiro ^a   Jia, Honge ^a   Hadano, Shingo ^a   Teraguchi, Masahiro ^a   Aoki, Toshiki ^a  

^a NIIGATA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; CATALYST ACTIVITY; DICHROISM; LIGANDS; MOLECULAR WEIGHT; MONOMERS;

ACHIRAL DIENE LIGANDS; CD SPECTRA; CHIRAL CONDITION; HELIX-SENSE-SELECTIVE POLYMERIZATION;

POLYMERIZATION;

EID: 35348819929     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma0713963     Document Type: Article

References (84)

1. For recent reviews, see: (a) Aoki, T. Prog. Polym. Sci. 1999, 24, 951.
2. (b) Feringa, B. L.; van Delden, R. A.; Koumura, N.; Geertsema, E. M. Chem. Rev. 2000, 100, 1789.
3. (c) Pu, L. Macromol. Rapid Commun. 2000, 21, 795.
4. (d) Cornelissen, J. J. L. M.; Rowan, A. E.; Nolte, R. J. M.; Sommerdijk, N. A. J. M. Chem. Rev. 2001, 101, 4039.
5. (e) Nakano, T.; Okamoto, Y. Chem. Rev. 2001, 101, 4013.
6. (f) Green, M. M.; Cheon, K.-S.; Yang, S.-Y.; Park, J.-W.; Swansburg, S.; Liu, W. Acc. Chem. Res. 2001, 34, 672.
7. (g) Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem. Rev. 2001, 101, 3893.
8. (h) Fujiki, M. Makromol. Chem., Rapid Commun. 2001, 22, 539.
9. (i) Yashima, E.; Maeda, K.; Nishimura, T. Chem-Eur. J. 2004, 10, 42.
10. (j) Aoki, T.; Kaneko, T.; Teraguchi, M. Polymer 2006, 47, 4867.
11. (a) Aoki, T.; Shinohara, K.; Oikawa, E. Makromol. Chem., Rapid Commun. 1992, 13, 565.
12. (b) Aoki, T.; Kokai, M.; Shinohara, K.; Oikawa, E. Chem. Lett. 1993, 2009.
13. (c) Shinohara, K.; Aoki, T.; Oikawa, E. Polymer 1995, 36, 2403.
14. (d) Aoki, T.; Shinohara, K.; Kaneko, T.; Oikawa, E. Macromolecules 1996, 29, 4192.
15. (e) Aoki, T.; Kobayashi, Y.; Kaneko, T.; Oikawa, E.; Yamamura, Y.; Fujita, Y.; Teraguchi, M.; Nomura, R.; Masuda, T. Macromolecules 1999, 32, 79.
16. (f) Shinohara, K.; Aoki, T.; Kaneko, T. J. Polym. Sci., Polym. Chem. Ed. 2002, 40, 1689.
17. (g) Teraguchi, M.; Suzuki, J.; Kaneko, T.; Aoki, T.; Masuda, T. Macromolecules 2003, 36, 9694.
18. (h) Aoki, T.; Fukuda, T.; Shinohara, K.; Kaneko, T.; Teraguchi, M.; Yagi, M. J. Polym. Sci., Polym. Chem. Ed. 2004, 42, 4502.
19. (i) Teraguchi, M.; Mottate, K.; Kim, S.-Y.; Aoki, T.; Kaneko, T.; Hadano, S.; Masuda, T. Macromolecules 2005, 38, 6367.
20. (j) Aoki, T.; Kaneko, T. Polym. J. 2005, 37, 717.
21. (a) Green, M. M.; Peterson, N. C.; Sato, T.; Teramoto, A.; Cook, R.; Lifson, S. Science 1995, 268, 1860.
22. (b) Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1997, 119, 6345.
23. (c) Nakashima, H.; Koe, J. R.; Torimitsu, K.; Fujiki, M. J. Am. Chem. Soc. 2001, 123, 4847.
24. (d) Shinohara, K.; Aoki, T.; Kaneko, T.; Oikawa, E. Polymer 2001, 42, 351.
25. (e) Miyagawa, T.; Furuko, A.; Maeda, K.; Katagiri, H.; Furusho, Y.; Yashima, E. J. Am. Chem. Soc. 2005, 127, 5018 and references therein.
26. (a) Ueno, A.; Takahashi, K.; Anzai, J.; Osa, T. J. Am. Chem. Soc. 1981, 103, 6410.
27. (b) Langeveld-Voss, B. M. W.; Janssen, R. A. J.; Christiaans, M. P. T.; Meskers, S. C. J.; Dekkers, H. P. J. M.; Meijer, E. W. J. Am. Chem. Soc. 1996, 118, 4908.
28. (c) Li, J.; Schuster, G. B.; Cheon, K.-S.; Green, M. M.; Selinger, J. V. J. Am. Chem. Soc. 2000, 122, 2603.
29. (d) Mayer, S.; Zentel, R. Macromol. Rapid Commun. 2000, 21, 927.
30. (e) Geng, Y.; Trajkovska, A.; Katsis, D.; Ou, J. J.; Culligan, S. W.; Chen, S. H. J. Am. Chem. Soc. 2002, 124, 8337.
31. (f) Oda, M.; Nothofer, H.-G.; Scherf, U.; Sunjic, V.; Richter, D.; Regenstein, W.; Neher, D. Macromolecules 2002, 35, 6792.
32. (g) Goto, H.; Yashima, E. J. Am. Chem. Soc. 2002, 124, 7943.
33. (h) Jaycox, G. D. J. Polym. Sci., Polym. Chem. Ed. 2004, 42, 566.
34. (i) Ohira, A.; Okoshi, K.; Fujiki, M.; Kunitake, M.; Naito, M.; Takahiro, H. Adv. Mater. 2004, 16, 1645.
35. (j) Agata, Y.; Kobayashi, M.; Kimura, H.; Takeishi, M. Polym. Int. 2005, 54, 260.
36. (k) Tabei, J.; Nomura, R.; Shiotsuki, M.; Sanda, F.; Masuda, T. Macromol. Chem. Phys. 2005, 206, 323.
37. (l) Onouchi, H.; Miyagawa, T.; Furuko, A.; Maeda, K.; Yashima, E. J. Am. Chem. Soc. 2005, 127, 2960 and references therein.
38. (a) Akagi, K.; Piao, G.; Kaneko, S.; Sakamaki, K.; Shirakawa, H.; Kyotani, M. Science 1998, 282, 1683.
39. (b) Hida, N.; Takei, F.; Onitsuka, K.; Shiga, K.; Asaoka, S.; Iyoda, T.; Takahashi, S. Angew. Chem., Int. Ed. 2003, 42, 4349.
40. (c) Yuan, G.-L.; Kuramoto, N. Macromol. Chem. Phys. 2004, 205, 1744.
41. (a) Kaneko, T.; Yamamoto, T.; Aoki, T.; Oikawa, E. Chem. Lett. 1999, 623.
42. (b) Murata, H.; Miyajima, D.; Nishide, H. Macromolecules 2006, 39, 6331.
43. Aoki, T.; Kaneko, T.; Maruyama, N.; Sumi, A.; Takahashi, M.; Sato, T.; Teraguchi, M. J. Am. Chem. Soc. 2003, 125, 6346.
44. Sato, T.; Aoki, T.; Teraguchi, M.; Kaneko, T.; Kim, S.-Y. Polymer 2004, 45, 8109.
45. Umeda, Y.; Kaneko, T.; Teraguchi, M.; Aoki, T. Chem. Lett. 2005, 34, 854.
46. Kaneko, T.; Umeda, Y.; Yamamoto, T.; Teraguchi, M.; Aoki, T. Macromolecules 2005, 38, 9420.
47. (a) Nolte, R. J. M.; van Beijnen, A. J. M.; Drenth, W. J. Am. Chem. Soc. 1974, 96, 5932.
48. (b) Deming, T. J.; Novak, B. M. J. Am. Chem. Soc. 1992, 1992, 7926.
49. (a) Okamoto, Y.; Suzuki, K.; Ohta, K.; Hatada, K.; Yuki, H. J. Am. Chem. Soc. 1979, 101, 4763.
50. (b) Okamoto, Y. J. Polym. Sci., Polym. Chem. Ed. 2004, 42, 4480 and references therein.
51. (a) Tian, G.; Lu, Y.; Novak, B. M. J. Am. Chem. Soc. 2004, 126, 4082.
52. (b) Tang, K-Z.; Boyle, P. D.; Novak, B. M. J. Am. Chem. Soc. 2005, 127, 2136.
53. Kamer, P. C. J.; Nolte, R. J. M.; Drenth, W. J. Am. Chem. Soc. 1988, 110, 6818.
54. (a) Nakano, T.; Okamoto, Y.; Hatada, K. J. Am. Chem. Soc. 1992, 114, 1318.
55. (b) Nakano, T.; Shikisai, Y.; Okamoto, Y. Polym. J. 1996, 28, 51.
56. (a) Corley, L. S.; Vogl, O. Polym. Bull. (Berlin) 1980, 3, 211.
57. (b) Vogl, O. J. Polym. Sci., Polym. Chem. Ed. 2000, 38, 2623.
58. (a) Ito, Y.; Ohara, T.; Shima, R.; Suginome, M. J. Am. Chem. Soc. 1996, 118, 9188.
59. (b) Ito, Y.; Miyake, T.; Hatano, S.; Shima, R.; Ohara, T.; Suginome, M. J. Am. Chem. Soc. 1998, 120, 11880.
60. Yashima, E.; Maeda, K.; Okamoto, Y. Nature (London) 1999, 399, 449.
61. Kaneko, T.; Horie, T.; Asano, M.; Aoki, T.; Oikawa, E. Macromolecules 1997, 30, 3118.
62. Kaneko, T.; Horie, T.; Asano, M.; Matsumoto, S.; Yamamoto, K.; Aoki, T.; Oikawa, E. Polym. Adv. Technol. 2000, 11, 685.
63. Kaneko, T.; Horie, T.; Aoki, T.; Oikawa, E. Kobunshi Ronbunshu 2000, 57, 672.
64. Kaneko, T.; Asano, M.; Yamamoto, K.; Aoki, T. Polym. J. 2001, 33, 879.
65. Nakano, T.; Tsunematsu, K.; Okamoto, Y. Chem. Lett. 2002, 31, 42.
66. Kern, R. J. J. Polym. Sci., Polym. Chem. Ed. 1969, 7, 621.
67. (a) Furlani, A.; Licoccia, S.; Russo, M. V. J. Polym. Sci., Polym. Chem. Ed. 1986, 24, 991.
68. (b) Furlani, A.; Napoletano, C.; Russo, M. V.; Feast, W. J. Polym. Bull. (Berlin) 1986, 16, 311.
69. (c) Furlani, A.; Napolentano, C.; Russo, M. V.; Camus, A.; Marsich, N. J. Polym. Sci., Polym. Chem. Ed. 1989, 27, 75.
70. (a) Tabata, M.; Yang, W.; Yokota, K. Polym. J. 1990, 22, 1105.
71. (b) Yang, W.; Tabata, M.; Kobayashi, S.; Yokota, K.; Shimizu, A. Polym. J. 1991, 23, 1135.
72. (c) Tabata, M.; Yang, W.; Yokota, K. J. Polym. Sci., Polym. Chem. Ed. 1994, 32, 1113.
73. (d) Tabata, M.; Sadahiro, Y.; Nozaki, Y.; Inaba, Y.; Yokota, K. Macromolecules 1996, 29, 6673.
74. (a) Kishimoto, Y.; Eckerle, P.; Miyatake, T.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1994, 116, 12131.
75. (b) Kishimoto, Y.; Itou, M.; Miyatake, T.; Ikariya, T.; Noyori, R. Macromolecules 1995, 28, 6662.
76. (c) Kishimoto, Y.; Miyatake, T.; Ikariya, T.; Noyori, R. Macromolecules 1996, 29, 5054.
77. (d) Kishimoto, Y.; Eckerle, P.; Miyatake, T.; Kainosho, M.; Ono, A.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1999, 121, 12035.
78. (e) Tang, B. Z.; Poon, W. H.; Leung, S. M.; Leung, W. H.; Peng, H. Macromolecules 1997, 30, 2209.
79. (f) Saito, M. A.; Maeda, K.; Onouchi, H.; Yashima, E. Macromolecules 2000, 33, 4616.
80. (a) Misumi, Y.; Masuda, T. Macromolecules 1998, 31, 7572.
81. (b) Kanki, K.; Misumi, Y.; Masuda, T. Macromolecules 1999, 32, 2384.
82. (c) Misumi, Y.; Kanki, K.; Miyake, M.; Masuda, T. Macromol. Chem. Phys. 2000, 201, 2239.
83. (d) Miyake, M.; Misumi, Y.; Masuda, T. Macromolecules 2000, 33, 6636.
84. This helix-sense tunability due to the cod and nbd ligands was also observed for other achiral monomers which gave the corresponding optically active helical poly(phenylacetylene)s by the helix-sense-selective polymerization. The results will be discussed in more detail in a subsequent paper.